Selective recognition of alkanoates by a β-cyclodextrin flexibly capped with a chromophore

Kahee Fujita, Tadashi Ueda, Taiji Imoto, Iwao Tabushi, Namiko Toh, Toshitaka Koga

研究成果: Contribution to journalArticle査読

12 被引用数 (Scopus)

抄録

The association between 6-deoxy-6-(p-hydroxy-m-nitrophenacylthio)-β-cyclodextrin 1 and sodium n-alkanoate, sodium 2,2-dimethylpropionate, or sodium 3,3-dimethylbutyrate was investigated. Host-guest association was measured by means of electronic spectroscopy and circular dichroism spectroscopy and ascertained to be 1:1. The inclusion of 2,2-dimethylpropionate or butanoate marginally affected the circular dichroism spectrum of 1. The inclusion of 3,3-dimethylbutyrate, hexanoate, octanoate, decanoate, or dodecanoate, however, dramatically affected the spectrum of 1. The plots of molecular ellipticities of the inclusion complexes against the carbon number of the n-alkanoates were sigmoid. From these observations, the effective size of the guest molecule to push the chromophore in the cavity to the capping position was estimated. From the similarity of the spectrum of the octanoate-1 complex to that of 1-adamantanecarboxylate-1 complex, the carbon chain of octanoate appears to be folded in the cavity of the cyclodextrin.

本文言語英語
ページ(範囲)108-114
ページ数7
ジャーナルBioorganic Chemistry
11
2
DOI
出版ステータス出版済み - 6 1982

All Science Journal Classification (ASJC) codes

  • 生化学
  • 分子生物学
  • 創薬
  • 有機化学

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